Ammonia → tert-Butyl 4-(cyclopropylamino)piperidine-1-carboxylate

HRID 333420Notes

Reaction equation

HRID 333420 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH:15]1([NH2:18])[CH2:17][CH2:16]1.[BH3-]C#N.[Na+].N>C(O)C.C(O)(=O)C>[CH:15]1([NH:18][CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]2)[CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 69828CyclopropylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 2769591tert-Butyl 4-(cyclopropylamino)piperidine-1-carboxylateYield 79.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

1 g (5 mmol) of tert-butyl 4-oxopiperidine-1-carboxylate is dissolved in 40 mL of ethanol with 10% of acetic acid. 0.28 mL (4.2 mmol) of cyclopropylamine is added. After 30 minutes, 0.53 g (36 mmol) of NaBH3CN is added and the reaction medium is stirred for one hour at room temperature. The reaction is stopped by addition of aqueous ammonia solution and the organic products are then extracted with ethyl acetate. The organic phase is dried and then evaporated. The crude product obtained is chromatographed on silica gel (eluent: 55/45 heptane/ethyl acetate). 0.8 g of tert-butyl 4-cyclopropylamino-piperidine-1-carboxylate in the form of a colourless oil is obtained in a yield of 79%.

Workup

  1. extractionthe organic products are then extracted with ethyl acetate
  2. customThe organic phase is dried
  3. customevaporated
  4. customThe crude product obtained
  5. customis chromatographed on silica gel (eluent: 55/45 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-280883677a7b4631a61d34d7fc57a784
Source dataset
uspto-grants-2014_11
Patent number
US08877968B2

Reaction notes

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